Sodium methanethiolate → HCID 68866096, compound

HRID 1988255Notes

Reaction equation

HRID 1988255 reaction equation
[CH2:1]([O:8][C:9](=[O:43])[NH:10][CH:11]([CH2:31]OS(C1C(C)=CC=CC=1)(=O)=O)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:15]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:44][S-:45].[Na+]>C(O)C.CO>[CH2:1]([O:8][C:9](=[O:43])[NH:10][CH:11]([CH2:31][S:45][CH3:44])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:15]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 86760898HCID 86760898, compound

Product 1

HCID 68866096HCID 68866096, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-(4-benzyloxy-3-t-butylphenyl)-1-toluenesulfonyloxymethylethylcarbamic acid benzyl ester 2.4 g, 3.99 mmol) in ethanol (40 ml), a solution of sodium methanethiolate (560 mg, 7.99 mmol) in methanol (4 ml) was added and stirred at 40° C. for 3 hours. The mixture was evaporated under reduced pressure to remove the solvent, mixed with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=5:1), giving the titled compound (1.63 g, 86%).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customto remove the solvent
  3. additionmixed with a saturated aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-94d309cc1b194d0bbda2bdd76a15cad5
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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